DE2264284C2 - Verfahren zur Herstellung von Bindemitteln für Druckfarben - Google Patents
Verfahren zur Herstellung von Bindemitteln für DruckfarbenInfo
- Publication number
- DE2264284C2 DE2264284C2 DE2264284A DE2264284A DE2264284C2 DE 2264284 C2 DE2264284 C2 DE 2264284C2 DE 2264284 A DE2264284 A DE 2264284A DE 2264284 A DE2264284 A DE 2264284A DE 2264284 C2 DE2264284 C2 DE 2264284C2
- Authority
- DE
- Germany
- Prior art keywords
- resin
- phenol
- anhydride
- resins
- hydrocarbon resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 32
- 239000000976 ink Substances 0.000 title claims description 26
- 238000007639 printing Methods 0.000 title claims description 26
- 239000011230 binding agent Substances 0.000 title claims description 25
- 230000008569 process Effects 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229920005989 resin Polymers 0.000 claims description 93
- 239000011347 resin Substances 0.000 claims description 93
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 54
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 32
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000008064 anhydrides Chemical class 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 27
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000007859 condensation product Substances 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 17
- 229920001568 phenolic resin Polymers 0.000 claims description 16
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 12
- 239000011976 maleic acid Substances 0.000 claims description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 150000002989 phenols Chemical class 0.000 claims description 11
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000025 natural resin Substances 0.000 claims description 7
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 238000002844 melting Methods 0.000 description 47
- 230000008018 melting Effects 0.000 description 41
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 25
- 238000002474 experimental method Methods 0.000 description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- 229920003987 resole Polymers 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000005011 phenolic resin Substances 0.000 description 13
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 238000012986 modification Methods 0.000 description 10
- 230000004048 modification Effects 0.000 description 10
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000007646 gravure printing Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- -1 rosin Chemical class 0.000 description 7
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 150000002736 metal compounds Chemical class 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000001639 calcium acetate Substances 0.000 description 5
- 229960005147 calcium acetate Drugs 0.000 description 5
- 235000011092 calcium acetate Nutrition 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 4
- 239000002952 polymeric resin Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000004525 petroleum distillation Methods 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 150000002469 indenes Chemical class 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 150000000469 3,5-xylenols Chemical class 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/38—Block or graft polymers prepared by polycondensation of aldehydes or ketones onto macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Paints Or Removers (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2264284A DE2264284C2 (de) | 1972-12-30 | 1972-12-30 | Verfahren zur Herstellung von Bindemitteln für Druckfarben |
| GB5951873A GB1458219A (en) | 1972-12-30 | 1973-12-21 | Resins |
| BE139248A BE809087A (fr) | 1972-12-30 | 1973-12-27 | Procede de preparation de liants pour encres d'impression et produits obtenus |
| JP48144793A JPS5220881B2 (enrdf_load_stackoverflow) | 1972-12-30 | 1973-12-28 | |
| NL7317761.A NL155878B (nl) | 1972-12-30 | 1973-12-28 | Werkwijze voor de bereiding van voor drukinkten geschikte bindmiddelen. |
| IT32384/73A IT1002418B (it) | 1972-12-30 | 1973-12-28 | Processo per la produzione di le ganti per colori da stampa |
| FR7346722A FR2212406B1 (enrdf_load_stackoverflow) | 1972-12-30 | 1973-12-28 | |
| US05/702,204 US4197378A (en) | 1972-12-30 | 1976-07-02 | Process for the preparation of a modified hydrocarbon resin |
| US06/039,399 US4401791A (en) | 1972-12-30 | 1979-05-15 | Process for the preparation of a modified hydrocarbon resin |
| US06/397,886 US4506059A (en) | 1972-12-30 | 1982-07-13 | Process for the preparation of a modified hydrocarbon resin |
| JP59103773A JPS60106867A (ja) | 1972-12-30 | 1984-05-24 | 印刷インキ用バインダ−の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2264284A DE2264284C2 (de) | 1972-12-30 | 1972-12-30 | Verfahren zur Herstellung von Bindemitteln für Druckfarben |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2264284A1 DE2264284A1 (de) | 1974-07-18 |
| DE2264284C2 true DE2264284C2 (de) | 1982-05-27 |
Family
ID=5865855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264284A Expired DE2264284C2 (de) | 1972-12-30 | 1972-12-30 | Verfahren zur Herstellung von Bindemitteln für Druckfarben |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4401791A (enrdf_load_stackoverflow) |
| JP (2) | JPS5220881B2 (enrdf_load_stackoverflow) |
| BE (1) | BE809087A (enrdf_load_stackoverflow) |
| DE (1) | DE2264284C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2212406B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1458219A (enrdf_load_stackoverflow) |
| IT (1) | IT1002418B (enrdf_load_stackoverflow) |
| NL (1) | NL155878B (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2264284C2 (de) * | 1972-12-30 | 1982-05-27 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Bindemitteln für Druckfarben |
| DE3531242A1 (de) * | 1985-08-31 | 1987-03-05 | Hoechst Ag | Modifiziertes cyclopentadienharz, verfahren zu dessen herstellung und verwendung |
| DE3538549A1 (de) * | 1985-10-30 | 1987-05-07 | Hoechst Ag | Wasserverduennbares druckfarbenbindemittelsystem und dessen verwendung als druckfarbe |
| NL8702153A (nl) * | 1987-09-10 | 1989-04-03 | Dsm Resins Bv | Harssamenstelling en de toepassing hiervan in drukinktsamenstellingen. |
| JPH0813946B2 (ja) * | 1987-10-09 | 1996-02-14 | 日本石油株式会社 | 水なし平版印刷方法 |
| JPH021331U (enrdf_load_stackoverflow) * | 1988-06-15 | 1990-01-08 | ||
| DE3821507A1 (de) * | 1988-06-25 | 1989-12-28 | Hoechst Ag | Pastenfoermige pigmentpraeparationen, verfahren zu ihrer herstellung und ihre verwendung |
| JPH0262020U (enrdf_load_stackoverflow) * | 1988-10-28 | 1990-05-09 | ||
| DE59308297D1 (de) * | 1992-04-08 | 1998-04-30 | Hoechst Ag | Modifiziertes Cyclopentadienharz |
| US5514209A (en) * | 1993-05-04 | 1996-05-07 | Markem Corporation | Hot melt jet ink composition |
| DE4401362C2 (de) * | 1994-01-18 | 1997-12-11 | Roland Man Druckmasch | Verfahren und Rotationsdruckmaschine für indirekten Tiefdruck |
| WO1996028305A1 (en) * | 1995-03-13 | 1996-09-19 | Markem Corporation | Inks for ink jet printing |
| US5763565A (en) * | 1995-05-10 | 1998-06-09 | Arizona Chemical Company | Process for making self-gelled resin solutions for ink formulations |
| US5587007A (en) * | 1995-08-14 | 1996-12-24 | Arizona Chemical Company | Modified dicyclopentadiene resins |
| US5863319A (en) * | 1996-12-10 | 1999-01-26 | Markem Corporation | Thermally stable hot melt ink |
| US6372851B1 (en) | 2000-07-06 | 2002-04-16 | Eastman Chemical Resins, Inc. | Maleated liquid C5 hydrocarbon resins |
| DE10162771A1 (de) * | 2001-12-20 | 2003-07-10 | Solutia Germany Gmbh & Co Kg | Verwendung von plastifizierten Novolaken als Zusatz zu Kautschukmischungen |
| FR3146906A1 (fr) | 2023-03-23 | 2024-09-27 | IFP Energies Nouvelles | Procédé de traitement d’un mélange en phase aqueuse de composés comprenant des sucres à 5 et 6 atomes de carbone. |
| FR3146904A1 (fr) | 2023-03-23 | 2024-09-27 | IFP Energies Nouvelles | Procédé de traitement d’un mélange en phase aqueuse de composés comprenant des sucres à 5 et 6 atomes de carbone. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US245635A (en) * | 1881-08-16 | Cover for pails | ||
| DE563876C (de) * | 1928-05-27 | 1932-11-10 | Herbert Hoenel Dr | Verfahren zum Veredeln von Harzen, Wachsen, fetten OElen u. dgl. |
| US3468829A (en) * | 1964-10-31 | 1969-09-23 | Arakawa Rinsan Kagaku Kogyo Kk | Gravure ink for paper |
| JPS5017883B2 (enrdf_load_stackoverflow) * | 1972-05-17 | 1975-06-25 | ||
| JPS5717894B2 (enrdf_load_stackoverflow) * | 1972-12-09 | 1982-04-13 | ||
| DE2264284C2 (de) * | 1972-12-30 | 1982-05-27 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Bindemitteln für Druckfarben |
| JPS503355A (enrdf_load_stackoverflow) * | 1973-05-11 | 1975-01-14 |
-
1972
- 1972-12-30 DE DE2264284A patent/DE2264284C2/de not_active Expired
-
1973
- 1973-12-21 GB GB5951873A patent/GB1458219A/en not_active Expired
- 1973-12-27 BE BE139248A patent/BE809087A/xx not_active IP Right Cessation
- 1973-12-28 FR FR7346722A patent/FR2212406B1/fr not_active Expired
- 1973-12-28 IT IT32384/73A patent/IT1002418B/it active
- 1973-12-28 NL NL7317761.A patent/NL155878B/xx not_active IP Right Cessation
- 1973-12-28 JP JP48144793A patent/JPS5220881B2/ja not_active Expired
-
1979
- 1979-05-15 US US06/039,399 patent/US4401791A/en not_active Expired - Lifetime
-
1982
- 1982-07-13 US US06/397,886 patent/US4506059A/en not_active Expired - Fee Related
-
1984
- 1984-05-24 JP JP59103773A patent/JPS60106867A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4401791A (en) | 1983-08-30 |
| NL7317761A (enrdf_load_stackoverflow) | 1974-07-02 |
| US4506059A (en) | 1985-03-19 |
| JPS60106867A (ja) | 1985-06-12 |
| JPS5220881B2 (enrdf_load_stackoverflow) | 1977-06-07 |
| JPS629627B2 (enrdf_load_stackoverflow) | 1987-03-02 |
| IT1002418B (it) | 1976-05-20 |
| GB1458219A (en) | 1976-12-08 |
| DE2264284A1 (de) | 1974-07-18 |
| FR2212406A1 (enrdf_load_stackoverflow) | 1974-07-26 |
| JPS49101103A (enrdf_load_stackoverflow) | 1974-09-25 |
| FR2212406B1 (enrdf_load_stackoverflow) | 1978-02-10 |
| NL155878B (nl) | 1978-02-15 |
| BE809087A (fr) | 1974-06-27 |
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